Glufimet

Glufimet (developmental code name RGPU-238), also known as dimethyl 3-phenylglutamate hydrochloride, is a derivative of glutamic acid (glutamate) which was developed in Russia and is related to the γ-aminobutyric acid (GABA) derivative phenibut (3-phenyl-GABA).[1][2][3][4] It contains phenibut and glycine fragments in its chemical structure, has been described as a "GABA precursor", and is said to modulate the GABA and nitric oxide (NO) systems and to have antioxidant activity.[1][2][3][4] It has been suggested that metabotropic glutamate receptors may also play a role in the mechanism of action of glufimet.[4] Stress-protective effects have been described for glufimet in animals.[1][2][3]

Glufimet

Clinical data
Other names	RGPU-238; Dimethyl 3-phenylglutamic acid hydrochloride; Dimethyl 3-phenylglutamate hydrochloride; 1,5-Dimethyl (2S)-2-amino-3-phenylpentanedioate hydrochloride
Identifiers
IUPAC name dimethyl 2-amino-3-phenylpentanedioate;hydrochloride
CAS Number	651321-95-8
PubChem CID	78064435
ChemSpider	9646572
CompTox Dashboard (EPA)	DTXSID00799548
Chemical and physical data
Formula	C13H18ClNO4
Molar mass	287.74 g·mol^−1
3D model (JSmol)	Interactive image
SMILES COC(=O)CC(C1=CC=CC=C1)C(C(=O)OC)N.Cl
InChI InChI=1S/C13H17NO4.ClH/c1-17-11(15)8-10(12(14)13(16)18-2)9-6-4-3-5-7-9;/h3-7,10,12H,8,14H2,1-2H3;1H Key:YYGZEJCVUMTAMY-UHFFFAOYSA-N

References

1. Tyurenkov IN, Perfilova VN, Sadikova NV, Berestovitskaya VM, Vasil'eva OS (July 2015). "Effects of a New Glutamic Acid Derivative on Myocardial Contractility of Stressed Animals under Conditions of Nitric Oxide Synthesis Blockade". Bull. Exp. Biol. Med. 159 (3): 384–6. doi:10.1007/s10517-015-2969-7. PMID 26205724.
2. Perfilova VN, Popova TA, Prokofiev II, Mokrousov IS, Ostrovskii OV, Tyurenkov IN (June 2017). "Effect of Phenibut and Glufimet, a Novel Glutamic Acid Derivative, on Respiration of Heart and Brain Mitochondria from Animals Exposed to Stress against the Background of Inducible NO-Synthase Blockade". Bull. Exp. Biol. Med. 163 (2): 226–229. doi:10.1007/s10517-017-3772-4. PMID 28726197.
3. Perfilova VN, Sadikova NV, Prokofiev II, Inozemtsev OV, Tyurenkov IN (2016). "[Cardioprotective effect of the new derivative of glutamic acid - glufimet in acute immobilization-painful stress in animals of different ages]". Adv Gerontol (in Russian). 29 (1): 116–122. doi:10.1134/S2079057016030073. PMID 28423256.
4. Borisov AV, Prokofiev II, Mokrousov IS, Perfilova VN, Tyurenkov IN (December 2017). "Inhibition of the Expression of Inducible NO Synthase by Neuroactive Amino Acid Derivatives Phenibut and Glufimet In Vitro and Ex Vivo". Bull. Exp. Biol. Med. 164 (2): 177–180. doi:10.1007/s10517-017-3952-2. PMID 29181662.